5-(羟甲基)-2',3'-O-(异丙亚基)尿苷 | 3816-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(羟甲基)-2',3'-O-(异丙亚基)尿苷
• 英文名称: 2',3'-O-isopropylidene-5-hydroxymethyl-uridine
• 英文别名: 2',3'-O-isopropylidene-5-hydroxymethyluridine；5-hydroxymethyl-2',3'-O-isopropylideneuridine；5-hydroxymethyl-2',3'-isopropylidene-uridine；5-hydroxymethyl-O^2'_,O3'-isopropylidene-uridine；1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5-hydroxy-methyluracil；5-(hydroxymethyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione；1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(hydroxymethyl)pyrimidine-2,4-dione
• CAS: 3816-77-1
• 化学式: C₁₃H₁₈N₂O₇
• 分子量: 314.295
• InChiKey: HXPQPPUFFZZKIT-TURQNECASA-N

物化性质

• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃，干燥

制备方法与用途

5-（羟甲基）-2′，3′-O-(1-甲基亚乙基)尿苷是一种胸苷类似物。这类化合物能在复制的DNA中表现出插入活性，可用于标记细胞并追踪DNA合成过程。

反应信息

• 作为反应物：
  描述：

  5-(羟甲基)-2',3'-O-(异丙亚基)尿苷 在 吡啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 生成 5-methoxymethyluridine
  参考文献：
  名称：

  Synthesis of various substituted 5-methyluridines (xm 5 U) and 2-thiouridines (xm 5 s 2 U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine

  摘要：

  5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm(5)U) and 5-methyl-2-thiouridines (xm(5)s(2)U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.023
• 作为产物：
  描述：

  尿嘧啶核苷 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 生成 5-(羟甲基)-2',3'-O-(异丙亚基)尿苷
  参考文献：
  名称：

  2'，3'-didehydro-2'，3'-dideoxy-5-hydroxymethyluridine的替代合成路线

  摘要：

  描述了从5-甲基尿苷和尿苷开始的核苷类似物2'，3'-didehydro-2'，3'-dideoxy-5-hydroxymethyluridine的替代合成方法。

  DOI：

  10.1016/j.tetlet.2006.09.083

文献信息

• mt-tRNA Components: Synthesis of (2-Thio)Uridines Modified with Blocked Glycine/Taurine Moieties at C-5,1
  作者：Grazyna Leszczynska、Piotr Leonczak、Agnieszka Dziergowska、Andrzej Malkiewicz

  DOI：10.1080/15257770.2013.838261

  日期：2013.11.2

  5-carboxymethylaminomethyl(-2-thio)uridine (cmnm5(s2)U) and 5-taurinomethyl(-2-thio)uridine (τm5(s2)U) with a blocked amino acid function. 2-(Trimethylsilyl)ethyl and 2-(p-nitrophenyl)ethyl esters of glycine and 2-(2,4,5-trifluorophenyl)ethyl ester of taurine were selected as protection of carboxylic and sulfonic acid residues, respectively. The first synthesis of 5-formyl-2′,3′-O-isopropylidene-2-thiouridine

  在本文中，我们讨论了在三乙酰氧基硼氢化钠（NaBH（OAc）3）存在下，用甘氨酸或牛磺酸酯对5-甲酰基-2'，3'-O-异亚丙基（-2-硫基）尿苷进行氨基化还原胺化的有用性。用于合成天然线粒体（mt）tRNA组分5-羧甲基氨基甲基（-2-硫代）尿苷（cmnm5（s2）U）和5-牛磺基甲基（-2-硫代）尿苷（τm5（s2）U）氨基酸功能。分别选择甘氨酸的2-（三甲基甲硅烷基）乙酯和2-（对硝基苯基）乙酯和牛磺酸的2-（2,4,5-三氟苯基）乙酯作为羧酸和磺酸残基的保护剂。还报道了5-甲酰基-2'，3'-O-异亚丙基-2-硫尿苷的首次合成。
• Efficient Synthesis of 5-Hydroxymethyl Pyrimidines and their Nucleosides Using Microwave Irradiation
  作者：El S. El Ashry、Adel A.-H. Abdel-Rahman

  DOI：10.1055/s-2002-35592

  日期：——

  Hydroxymethylation of uracil (1), cytosine (3), 5-hydroxymethyl-2′,3′-O-isopropylideneuridine (5), 5′-O-tert-butyldiphenylsilyl-2′,3′-O-isopropylideneuridine (7), 2′,3′-O-isopropyl-idenecytidine (9) and 2′,3′-O-isopropylidene-5′-O-tritylcytidine (11) was efficiently carried out with paraformaldehyde in alkaline medium under microwave irradiation in very high yield.

  尿嘧啶（1）、胞嘧啶（3）、5-羟甲基-2′,3′-O-异亚丙基尿苷（5）、5′-O-叔丁基二苯基硅-2′,3′-O-异亚丙基尿苷（7）、2′、9）和 2′,3′-O-异亚丙基-5′-O-三苯甲基胞苷（11）。
• Site-selected incorporation of 5-carboxymethylaminomethyl(-2-thio)uridine into RNA sequences by phosphoramidite chemistry
  作者：Grazyna Leszczynska、Jakub Pięta、Karolina Wozniak、Andrzej Malkiewicz

  DOI：10.1039/c3ob42302f

  日期：——

  report the first site-selected incorporation of cmnm5U and cmnm5s2U into RNA sequences by phosphoramidite chemistry on a CPG solid support. Trifluoroacetyl and 2-(trimethylsilyl)ethyl were selected for the protection of the amine and carboxyl functions, respectively.

  5-羧甲基氨基甲基尿苷（cmnm 5 U）和5-羧甲基氨基甲基-2-硫尿苷（cmnm 5 s 2 U）位于几个胞质和线粒体tRNA序列的摆动位置。在本文中，我们报告了通过CPG固体支持物上的亚磷酰胺化学方法将cmnm 5 U和cmnm 5 s 2 U首次定点掺入RNA序列。选择三氟乙酰基和2-（三甲基甲硅烷基）乙基分别用于保护胺和羧基官能团。
• Post-synthetic conversion of 5-pivaloyloxymethyluridine present in a support-bound RNA oligomer into biologically relevant derivatives of 5-methyluridine
  作者：Karolina Bartosik、Elzbieta Sochacka、Grazyna Leszczynska

  DOI：10.1039/c6ob02674e

  日期：——

  A reliable post-synthetic method to access the modified RNA oligomers containing biologically important 5-methyluridines: mnm⁵U, cmnm⁵U, τm⁵U, nm⁵U, inm⁵U and cnm⁵U.

  一种可靠的后合成方法，用于制备含有生物学重要的5-甲基尿嘧啶修饰的RNA寡核苷酸：mnm5U，cmnm5U，τm5U，nm5U，inm5U和cnm5U。
• Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif
  作者：Kohji Seio、Takeshi Wada、Kensaku Sakamoto、Shigeyuki Yokoyama、Mitsuo Sekine

  DOI：10.1021/jo971797o

  日期：1998.3.1

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.